Synthesis of 2',3'-dihydrosolanesyl analogues of β-D-arabinofuranosyl-1-monophosphoryldecaprenoI with promising antimycobacterial activity

被引:24
作者
Bosco, Michael
Bisseret, Philippe
Constant, Patricia
Eustache, Jacques
机构
[1] Univ Haute Alsace, Ecole Natl Super Chim Mulhouse, CNRS, Lab Chim Organ & Bioorgan Assoc, F-69093 Mulhouse, France
[2] CNRS, UMR 5089, Inst Pharmacol & Biol Struct, F-31077 Toulouse 4, France
关键词
D O I
10.1016/j.tetlet.2006.10.151
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new hydrolytically stable analogues of beta-D-arabinofuranosyl-1-monophosphoryldecaprenol, the donor substrate for mycobacterial arabinosyltransferase, have been prepared. Biological evaluation of these compounds in vitro against Mycobacterium tuberculosis H(37)Rv strain revealed a promising activity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:153 / 157
页数:5
相关论文
共 15 条
[1]   Direct colorimetric assay for rapid detection of rifampin-resistant Mycobacterium tuberculosis [J].
Abate, G ;
Aseffa, A ;
Selassie, A ;
Goshu, S ;
Fekade, B ;
WoldeMeskal, D ;
Miörner, H .
JOURNAL OF CLINICAL MICROBIOLOGY, 2004, 42 (02) :871-+
[2]   2,3,5-TRI-O-BENZYL-D-RIBOSYL AND -L-ARABINOSYL BROMIDES [J].
BARKER, R ;
FLETCHER, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4605-&
[3]   Synthesis of (difluoromethyl)phosphonate azasugars designed as inhibitors for glycosyl transferases [J].
Behr, JB ;
Evina, CM ;
Phung, N ;
Guillerm, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1597-1599
[4]   Synthesis of sugar-derived phostones by activation of γ-hydroxyphosphonic acids [J].
Bosco, M ;
Bisseret, P ;
Eustache, J .
TETRAHEDRON LETTERS, 2003, 44 (11) :2347-2349
[5]   A new concise synthesis of nectrisine and its facile conversion to phosphonoazasugars [J].
Bosco, M ;
Bisseret, P ;
Bouix-Peter, C ;
Eustache, J .
TETRAHEDRON LETTERS, 2001, 42 (45) :7949-7952
[6]   Sulfone and phosphinic acid analogs of decaprenolphosphoarabinose as potential anti-tuberculosis agents [J].
Centrone, CA ;
Lowary, TL .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (21) :5495-5503
[7]   Synthesis and antituberculosis activity of C-phosphonate analogues of decaprenolphosphoarabinose, a key intermediate in the biosynthesis of mycobacterial arabinogalactan and lipoarabinomannan [J].
Centrone, CA ;
Lowary, TL .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8862-8870
[8]   Biosynthesis of the arabinogalactan-peptidoglycan complex of Mycobacterium tuberculosis [J].
Crick, DC ;
Mahapatra, S ;
Brennan, PJ .
GLYCOBIOLOGY, 2001, 11 (09) :107R-118R
[9]   Synthesis of new (difluoromethylphosphono)azadisaccharides designed as bisubstrate analogue inhibitors for GlcNAc:β-1,4 glycosyltransferases [J].
Gautier-Lefebvre, I ;
Behr, JB ;
Guillerm, G ;
Ryder, NS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (13) :1483-1486
[10]   FARNESYL CHAIN MODIFICATION OF SQUALENE SYNTHASE INHIBITOR BENZYLFARNESYLAMINE - CONVERSION TO THE TERMINAL BIS(TRIFLUOROMETHYL) DERIVATIVE [J].
JEWELL, CF ;
BRINKMAN, J ;
PETTER, RC ;
WAREING, JR .
TETRAHEDRON, 1994, 50 (13) :3849-3856